Miticidal active fluoro phthalimide derivatives

ABSTRACT

1. A COMPOUND OF THE STRUCTURE:   1,3-DI(O=),2-(F-C(-CL)2-C(-CL)2-S-)-4,7-DIHYDROISOINDOLINE

United States Patent Office oififaiii EXAMPLE 1. MITICIDAL N-(Z-fluoro-l,1,2,2-tetrachloroethylthio)-tetrahydro DERIVATIVES phthallmide 1 Baker, 0mm, -I and Peter F. Epstein, A first material was prepared by mixing together 100 Prairie Village, Kans., asslgnors to Stauifer Chemical 5 ml. water and 12.6 (0.05 moles) of 1,1,2,2-tetrachloro- Company, New York, N.Y

2 fiuoroethylsulfenyl chloride. Then, asecond solution No Drawmg' N containing 7.5 g. (0.05 moles) of .tetrahydro phthalimide US. z6o 326 H 2 Claims and 2.0 g. (0.05 moles) sodium hydroxide and 100 ml.

10 of water were mixed together. The second solution was then added to the first over a period of five minutes at 10- ABSTRACT OF THE DISCLOSURE C. with stirring and cooling. A solid formed and the N compounds h h i i id l i i are d mixture was stirred for 30 minutes, when 100 ml. of scribed hereim These compounds u 1 chloroform was added. The chloroform solution was dried 15 over magnesium sulfate and evaporated in vacuum to yield 9 g. of a yellow oil. On standing, crystals formed. Then, 10 m1. of n-pentane was added and the crystals filtered OE and washed with additional n-pentane to yield ii 3.0 g. of crystals having a m.p. of 110-115 C. 01 31 EXAMPLE 2 l N-S-t!!CF N-(2-fluoro-1,1,2,2-tetrachloroethylthio)-phthalimide 1 1 To a suspension of 18.5 g. (0.1 moles) potassium phthalimide in 200 ml. of benzene was added a solution of 25.3 g. (0.1 moles) of 2-fluoro-1,1,2,2-tetrachloroethyland a p ene-l-sulfenyl chloride in 50 ml. of benzene. The reaction was exothermic and the temperature was maintained below C. After the addition of the components, the

C1 c1 mixture was warmed to 70 C. and allowed to stand over- 30 night. The benzene was removed under reduced pressure N- and the residue dissolved in mixed chloroform and water.

/ 1 l The chloroform layer was evaporated, washed twice with c a cold sodium hydroxide solution and twice with water, 8 dried over sodium sulfate, filtered and stripped. A white DESCRIPTION OF THE INVENTION was ENTOMOLOGICAL TESTING METHODS Th s invention is directed t0 novel compounds which The compounds of the present invention were tested to y be generally described as flouro Phfllalimide defiva- 40 show activity against two-spotted mites as follows: Pinto tives which are active miticides. The compounds of the beans (Phaseolus sp.) plants, approximately 23 inches present invention are as follows: tall, were transplanted into sandy loam soil in 3" clay pots and infested with 50-75 aphids of mixed ages.

Twenty-four hours later they were sprayed, to the point of run-oil, with aqueous suspension of the toxicant. Aliquots of the toxicant, dissolved in appropriate solvent,

are diluted in water to which has been added 0.0002% C1 01 of a conventional wetting agent such as a polyoxy-ethylb ene sorbitan monolaurate ether of alkylated phenolic phe- I J nols blended with organic sulfonates. Test concentrations 1 1 ranged from 0.05% to that at which 50% mortality is obtained. Mortality is recorded after forty-eight hours and the LD values are expressed as percent active in- 35 solid was formed, having a m.p. of 147-149 C. The

and gredients in the aqueous suspensions. The results of these I tests are tabulated below.

/ 1 I LB values 0 [Two-spotted mites] g Compound P.E., Eggs, number Structure percent percent by reacting an appropriate phthalimide compound with an appropriate fluoro sulfenyl chloride to produce the end H 01 In general, the above two compounds can be prepared (1 product. g

In order to illustrate the merits of the present invention the following examples are provided: See footnom at end of table.

tivityi ih'ose ohtzi iriedinfthe prior aft- Compounds No.

1 and 3.

01 1. A compound of the structure 5 3 e 6 .2 T F m n" 1 1 E n l am I m o m .m P n C S S s E wTmn .\N.. mm mm P. 0 0 6 0 .mSHK R 25 E6% mm 54 U 87 84 600 37 01 3 3 5 0 5 1 2 2 0 5 0 J m w m m w m n w m m w m 5 0 0 0 0 4 JOSEPH A. NARCAVAGE, Primary Examiner See US. Pat. No. 3,178,447.

R X Q S U 4 7 H 2 4 

1. A COMPOUND OF THE STRUCTURE: 